PERFLUOROOCTYLATION OF AROMATIC-COMPOUNDS WITH PERFLUOROAZOOCTANE UPON 185 NM IRRADIATION IN A 2-PHASE SYSTEM

An efficient method for the preparation of perfluorooctylated aromatic and heteroaromatic compounds has been developed using photolysis of p erfluoroazooctane (E)-1 upon 185 mm irradiation. The use of a two-phas e system made up of a perfluorohexane solution of (E)-1 and a suitable aromatic compound has proved efficient for this reaction. The photoly tic mechanism of(E)-1 upon 185 nm irradiation has also been investigat ed on the basis of quantum yield, light intensity dependence and UV-VI S spectra. It is shown that (E)-1 is photoisomerized by one photon abs orption to the (Z)-isomer, with subsequent extrusion of nitrogen by a second photon absorption.